Palifosfamide-Tris
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MedKoo CAT#: 202130

CAS#: 1070409-31-2 (tris salt)

Description: Palifosfamide, also known as ZIO201, is a synthetic mustard compound with potential antineoplastic activity. An active metabolite of ifosfamide covalently linked to the amino acid lysine for stability, palifosfamide irreversibly alkylates and cross-links DNA through GC base pairs, resulting in irreparable 7-atom inter-strand cross-links; inhibition of DNA replication and cell death follow. Unlike ifosfamide, this agent is not metabolized to acrolein or chloroacetaldehyde, metabolites associated with bladder and CNS toxicities. In addition, because palifosfamide does not require activation by aldehyde dehydrogenase, it may overcome the tumor resistance seen with ifosfamide.


Chemical Structure

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Palifosfamide-Tris
CAS# 1070409-31-2 (tris salt)

Theoretical Analysis

MedKoo Cat#: 202130
Name: Palifosfamide-Tris
CAS#: 1070409-31-2 (tris salt)
Chemical Formula: C8H22Cl2N3O5P
Exact Mass:
Molecular Weight: 342.15
Elemental Analysis: C, 28.08; H, 6.48; Cl, 20.72; N, 12.28; O, 23.38; P, 9.05

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Related CAS #: 1070409-31-2 (tris salt); 31645-39-3 (free acid)  

Synonym: ZIO201; ZIO-201; ZIO 201; IPAM; NSC 297900; NSC-297900; NSC297900; isophosphoramide mustard; Palifosfamide. Palifosfamide tris salt; Trade name: Zymafos.

IUPAC/Chemical Name: N,N'-Bis(2-chloroethyl)phosphorodiamidic acid

InChi Key: BKCJZNIZRWYHBN-UHFFFAOYSA-N

InChi Code: InChI=1S/C4H11Cl2N2O2P/c5-1-3-7-11(9,10)8-4-2-6/h1-4H2,(H3,7,8,9,10)

SMILES Code: O=P(NCCCl)(NCCCl)O.NC(CO)(CO)CO

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not soluble in water.

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 342.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Williams R. Discontinued in 2013: oncology drugs. Expert Opin Investig Drugs. 2015 Jan;24(1):95-110. Epub 2014 Oct 14. PubMed PMID: 25315907.

2: Movva S, Verschraegen C. Systemic management strategies for metastatic soft tissue sarcoma. Drugs. 2011 Nov 12;71(16):2115-29. doi: 10.2165/11594500-000000000-00000. Review. PubMed PMID: 22035513.

3: Jones B, Komarnitsky P, Miller GT, Amedio J, Wallner BP. Anticancer activity of stabilized palifosfamide in vivo: schedule effects, oral bioavailability, and enhanced activity with docetaxel and doxorubicin. Anticancer Drugs. 2012 Feb;23(2):173-84. doi: 10.1097/CAD.0b013e32834d73a6. PubMed PMID: 22027537.

4: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2009 Dec;31(10):661-700. PubMed PMID: 20140276.

5: Jung S, Kasper B. Palifosfamide, a bifunctional alkylator for the treatment of sarcomas. IDrugs. 2010 Jan;13(1):38-48. Review. PubMed PMID: 20024846.

6: Hingorani P, Zhang W, Piperdi S, Pressman L, Lin J, Gorlick R, Kolb EA. Preclinical activity of palifosfamide lysine (ZIO-201) in pediatric sarcomas including oxazaphosphorine-resistant osteosarcoma. Cancer Chemother Pharmacol. 2009 Sep;64(4):733-40. doi: 10.1007/s00280-008-0922-4. Epub 2009 Feb 18. PubMed PMID: 19224214.

7: Anderson P, Aguilera D, Pearson M, Woo S. Outpatient chemotherapy plus radiotherapy in sarcomas: improving cancer control with radiosensitizing agents. Cancer Control. 2008 Jan;15(1):38-46. Review. PubMed PMID: 18094659.



Additional Information

Palifosfamide (ZIO-201) is currently developed by ZIOPHARM Oncology, Inc. It is  a proprietary stabilized metabolite of ifosfamide. Ifosfamide has been shown to be effective in high doses in treating testicular cancer, sarcoma and lymphoma. Ifosfamide-based treatment generally represents the standard of care for sarcoma; however, it is not approved by the FDA in this indication. Ifosfamide metabolites include acrolein and chloroacetaldehyde, both highly toxic.  Preclinical studies have shown that palifosfamide has activity in leukemia and solid tumor cancers. These studies also indicate that palifosfamide has a better safety profile than ifosfamide, likely because the toxic metabolites of ifosfamide, acrolein and chloroacetaldehyde are not present in palifosfamide. We believe the administration of palifosfamide may avoid many of the toxicities of ifosfamide without compromising the activity of the drug. see ZIOPHARM's website:  http://www.ziopharm.com/clinical_zio201.php.